10 Guests Who Trolled David Letterman

There's probably a show business rule about not biting the hand that rolls your movie clip on national television. But given that David Letterman, whose CBS program Late Show turns twenty today, is as responsible as anyone on television for making irreverence an art form, it's not surprising that he's had to contend with some unexpected on-air sparring partners from time to time. Our favorite among these seem to possess sincerity but funnel it, much to Dave's bemusement or glee, through grumpiness, subtle contempt, pharmaceuticals, or all of the above, resulting in live-to-tape gems. With two decades of Late Show on the books and more than 30 years overall of Letterman on late-night programming (and because Terry Gross is talking about it), Vulture had an excuse to look back at some of the best Letterman guests who didn't seem to be playing along.

Quentin Tarantino (1997)Maybe he needed to remember where he was; maybe he spilled spaghetti sauce on his tuxedo backstage. Either way, wearing a Late Show T-shirt (shot out of a cannon?) qualifies Tarantino as a Letterman troll solely for fashion reasons — although forgetting that the taped program would actually be airing after Christmas doesn't hurt, either.

Kristen Stewart (2008)Kristen Stewart is a walking raised middle finger. And for whatever may have slipped her mind during this interview, she never forgot the most important maxim: When in need of something to say on Late Show With David Letterman, express that need out loud. After this interview, Vegas odds were 3:1 that she'd make it to Yale and later found the Department of Kristen Stewart Studies.

Chloë Sevigny (1998)If every other 23-year-old were high while watching this, then good on her for joining the club. Also, calling yourself a cinephile on the air, or expressing any regard for art, is a worthy way to shut the crowd up — elderly folks from Indianapolis didn’t drive to New York to hear that kind of stuff. And speaking of old people, why not call out your great-aunt’s lingering hatred of the Japanese?

Tom Waits (1988)Another maxim: Real men don’t smile on Late Night With David Letterman. This feels like Tom Waits winning a staring contest without even looking anyone in the eye. One can hope that he really did abuse a CBS expense account for the making of this episode.

Cybill Shepherd (1986)The difference between trolling and floundering — that is, the difference between Cybill Shepherd and Madonna — is the ability to piss off Dave without completely alienating the audience. There may or may not be a reference at 8:42 to keeping Ted Kennedy out of a Cybill Sandwich. Either way, he didn’t play her clip, so cheers!

Sandra Bernhard (1983)Sandra Bernhard’s been the most exasperating recurring guest on Letterman who’s yet to be banned — her tantrums ping-pong between the 12-year-old and 70-year-old varieties. The ’83 clip wins for the Elvis rendition at the start, at the poignant song title.

Crispin Glover (1990)Joaquin Phoenix’s I’m Still Here performance art disqualifies him as a Letterman foil in retrospect, and Andy Kaufman's many purposefully off-putting appearances made the unexpected a little too expected. Looking back, even Crispin Glover’s infamous firsttwo cracks at Late Night were ham-handed, if still commendably weird. But George McFly's third go is impressive. Stammering and pausing are two easy ways to threaten live tapings, but these monologues are borderline lucid and the “Clowny Clown Clown” suit only enhances the experience.

Howard Stern (1985) They developed a friendship, or at least mutual appreciation, over time, but this Howard Stern appearance from 1985 spooked Dave a little bit. Stern basically comes on Late Night to resume whatever he'd been talking about on his radio program that morning. The effect is that it's like he's playing a video game where the goal is to see how much hate mail he can elicit before the buzzer sounds.

Harmony Korine (1995)Did the Letterman bookersstart watching Kids, get twenty minutes in, and think, Let’s have the person responsible for it come on network television to talk about it? They — we all — should be grateful for the priceless one-sided exchanges that ensued when the 22-year-old debut filmmaker made his first appearance on Late Show, especially Letterman's bemused reactions after Korine tells a non sequitur joke ("this guy said that his luck was so bad that aspirin gave him headaches") and a non sequitur anecdote about a man who "got a shish kebab skewer stuck through his ass cheeks."

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